Water-insoluble azo dyestuffs



Patented Mar. 8, 1938 UNITED STATES PATENT OFFICE WATER-INSOLUBLE AZO DYESTUFFS Fritz Ballauf, Cologne-Holweide, and Otto Bayer, Leverkusen I. G.-Werk, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application August 31, 1936, Serial No. 98,736. In Germany September 7, 1935 Claims.

The present invention relates to water-insoluble azodyestuffs and to fibers dyed therewith, more particularly it relates to Water-insoluble azodyestuffs which may be represented by the fol- 5 lowing general formula:

SO2NR N=N-Rf In: the said formula R stands for the radical of a hydrocarbon which may bear substituents, such as alkyl, hydroxy-alkyl, phenyl, chlorophenyl', methyl-phenyl, methoXy-phenyl and the like, and R stands for the radical of an aryl amide of an aromatic ortho-hydroxycarboxylic acid.

Our new dyestuifs are obtainable by diazotizing an amine of the general formula:

in which R means the same as stated above and coupling in substance or on substratum, especial- 1y on vegetable fibers, with an aryl amide of an aromatic ortho-hydroxycarboxylic acid,ther'eby The invention is illustrated by the following examples: I Example 1 grams of cotton yarn are grounded for half an hour in 1000 cos. of an aqueous solution alkaline with soda prepared in the usual manner from 5 grams of 2.3-hydroxynaphthoylamino-2- methyl-4-methoxybenzene. The yarn is then centrifuged, and the dyeing is developed in 1000 cos. of a diazo bath at 40 C. prepared in the usual manner by diazotizing 2.4 grams of the amine of the formula:-

and neutralizing with sodium acetate; thereupon the yarn is rinsed, soaped and dried. A deep blue of good fastness to light, to boiling and to 2 chlorine is thus obtained. Y

The dyestuff corresponds to the following formula:

SOr-N-OH:

$11 doNHOoord I CH3 Example 2 24 grams of 4-amino-N-methylnaphthosultam are diazotized in the known manner. The diazo solution is then introduced into an alkaline solution prepared from 31 grams of 2.3-hydroxynaphthoylamino- 2 methyl- 4 -methoxybenzene. The reaction mixture is then rendered acid with acetic acid, and the dyestuif separated is filtered off. A reddish blue powder is thus obtained.

The dyestuff corresponds to the following for mula:

Example 3 24 grams of 4-amino-N-methylnaphthosultam are converted in the known manner; e. g. with sarcosine, into a watersoluble diazoamino compound and mixed with 31 grams of 2'.3-hydroxynaphthoylamino 2 -methyl- 4 -methoxybenzene. By adding 380 cos. of water, grams of Turkey red oil and 30 grams of caustic soda lye 32% both products are dissolved. Thereupon 500 grams of a starch tragacanth thickener are stirred in. The cotton printed with this solution is dried and then treated with an acid in the form of a vapour or liquid, developed and soaped. A reddish blue is thus obtained.

The dyestuff corresponds to the following for- 0H JJO-NH-O-OCH:

In an analogous manner there is obtained by using the method above described:

By combination oi- With- 2.3-hydroxynaphthoylamino- 4 amino N methyl A blue 2-methylbenzene. naphthosultaml 2.3-hydroxynaphthoylammodo A red- 2-methyli-methoxybenzene. gli s h ue 2.3-hydroxynaphthoylaminodo A blue 2-methyl-5-chlorobenzene. 2.3-hydrox,ynaphthoylaminodo A bluish 2.4-d1methoxy5-ehlor0benviolet. zone 22 3 hydroxynaphthoylamdo Ablue mo-2-ehlorobenzene V 2.3-hydroxynaphthoylam1nod0 Ablue 4-methoxybenzene 2.3-hydroxynaphthoylaminodo A red- E-methoxybenzene d i s 11 blue 2fl-hydlgolxynaphthoylaminodo Ablue -nap a one 7.8 benzo 2 '.3 hydroxy do A dark $arbazoylam1no-4-methoxyblue enzene 2.3-hydroxynaphth0ylamin0- 4-amino-N-hydroxyeth- A blue A-methoxybenzene yl-naphthosultam 2i3-hy%%xynaphthoylaminodo Ablnavy -nap a ene ue 7.8 benzo 2 .3 hydroxy do A navy carbazoylammo-i-methoxyblue benzene 2.3-hydroxynaphthoylamino- 4 amino N -n propyl- A bluish %.4 dnnethoxy 5 chloro naphthosultam corinth enzene. 2i3 hfi droynaphtholyaminodo A blu i fi -e oxy enzene corm 2.3-hydroxynaphthoylaminodo A bluish 2-methy14-methoxybenzene. eorinth 2.3-hyd:3inaphthoylam1nodo Ablnavy a-nap a one. no 2ghy%l%xynaphthoylaminodo Abl dark -nap a ene. ue. 7.8 benzo 2 23 hydroxy do A blackgubazoylammoA-methoxyish blue enzene.

By combination oi With 2.3-hydroxynaphthoylamino- 4 amino N ethyl- A dark a-naphthalene. nephthosultam. ue 2.3-hydroxynaphthoylamino- 4 amino N n butyl- A 0 o r benzene. naphthosultam. inth 2.3hydroxynaphthoylaminodo A hl s 2.4 dimethoxy 5 chlorocorlnth benzene.

2.3-hydroxynaphthoylamino- 2-methyl-4-chlorobenzene.

2.3-hydroxynaphthoylamino- 2-methoxy-i-chlorobenzene.

.3-hydroxynaphthoylaminod0. A r d- 2-methylbenzene. d i s h corinth 2.3-hydr0xynaphthoylaminodo A d Qmaphthalene. brown '-3-hyd1'0Xynaphthoylaminodo A navy 3-n1trobenzene. ue

7.8 b81120 2.3' hydroxyd0 A navy %arbazoylaminoi-methoxyenzene.

2.3-hydroxynaphthoylamino- 4 amino N n y A bluish 2-n1etbyl-4methoxybenzene. naphthosultam. vlolet 2.3-hydroxynaphthoylamino- .do A cor- 2-methoxy-5-chlorobenzene. mill 2 y roxycarbazole 3 ea do A red boxylic aoid--chloro-anilide. d i S h brown 2.3"-hydroxynaphth0y1- do A bluish am1no-2-naphthalene. violet 2.3;hydroxynaphthoy1- .do A bluish immo 4- ehloro 2 methyl Violet enzene.

7.8 benzo 2'3 hydroxydo A bluish garbazoylaminoA-methoxy blac enzene.

7.8 benzo 2'3 hydroxydo A bluish carbazoylamino 2 methylblae l-methoxybenzene.

2.3-hydroxynaphthoylamino- 4-amino-N-(p-anisyh- A r e d 2.5 dimethoxy 4 chloronaphthosultam. d i s h benzene. corinth 2.3-hydroxynaphthoylaminodo A bluis 2 methyl 4 methoxy bencorintb zene.

2.3-hydroxynaphthoylaminodo A re d l-naphthalene. d i s h corinth 7.8 benzo 2.3 hydroxydo Ablack garbazoylaminoA-methoxyenzene.

7.8 benzo 2.3 hydroxydo A bluish oarbazoylamino 2 methylblack 4-methoxybenzene.

We claim: 1. Water-insoluble azodyestufis of the general formula:

wherein R stands for the radical of a hydrocarbon, and R stands for a radical selected from the group consisting of aryl amides of 2.3-hydroxynaphthoic acid and benzocarbazole-ortho-hydroxycarboxylic acid, yielding when produced on the fiber in general deep shades of good fastness properties.

2. Water-insoluble azodyestufis of the general formula:

wherein R stands for the radical of a 2.3-hydroxynaphthoic acid aryl amide, yielding when produced on the fiber in general deep shades of good fastness properties.

3. Water-insoluble azodyestufl's of the general formula:

SOB-N-OHZ H comm-Q2:

wherein one X stands for a methoxy group and the other X stands for hydrogen, yielding when produced on the fiber, blue shades of good fastness properties.

5. The water-insoluble azodyestuff of the formula:

yielding when produced on the fiber blue shades of good fastness properties.

6. Fibers dyed with a dyestufi as claimed in claim 1.

7. Fibers dyed with a dyestuff as claimed in claim 2.

8. Fibers dyed with a dyestuif as claimed in claim 3.

9. Fibers dyed with a dyestuff as claimed in claim 4.

10. Fibers dyed with a dyestuif as claimed in claim 5.

FRITZ BALLAUF. OTTO BAYER. 

